Do I Even Want to Date Again? How to Figure Out What You Really Want

“Do I want to date again? Is it worth the effort at 68 years old?” I answer this dating dilemma here and on the podcast.

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I’m so excited to introduce something new here at Last First Date: Dating Dilemmas. Readers and listeners submit their real dating questions and dilemmas, and I answer a selection of them right here on the blog, and on Last First Date Radio as video and audio episodes. If you have a dating dilemma you’d love answered, submit yours here: https://tinyurl.com/datingdilemma

Our first Dating Dilemma comes from a woman who sent in this question:

“How do I determine if I even want to date or have another relationship? 68 years old, two marriages (24 and 10 years). A few long term relationships. Last one ended over a year ago. I am financially secure and have some good friends. Like having my own space. I do miss intimacy but that is not guaranteed with men in my age range. Every time I start to prepare to go on the apps I end up thinking it’s not worth the effort. I don’t know if I’m being realistic or just scared.”

What’s the Real Question?

There’s a big difference between “Do I want to date?” and “Am I afraid to date?”

Both can be true at the same time. Fear and frustration can look almost identical from the inside, which is exactly why this woman doesn’t know which one is driving her. That confusion isn’t a weakness. It’s actually a sign of self-awareness. She knows something is going on, she just hasn’t untangled it yet.

So let’s start there.

What Your Resistance Is Telling You

When you sit down to open a dating app and your whole body says no, that’s information. The question is: what is it telling you?

It might be a reality check. After two marriages and several long-term relationships, you know what partnership feels like and what the wrong relationship actually costs. You’ve lived through the compromises, the communication work, the adjustments to your space and routines. There’s nothing wrong with deciding that the tradeoffs aren’t worth it to you right now, or ever.

It might be self-protection. After a relationship ends, your nervous system doesn’t forget. Putting yourself out there again means risking loss again, and if part of you is still recovering even a year later, it makes sense that you’d be resisting dating again. You’re protecting yourself from getting hurt again.

It might be grief about the dating landscape at this age. She named it herself: intimacy isn’t guaranteed with men her age. That’s a real and painful thing to reckon with. The dating pool of truly eligible partners is smaller. Health issues, emotional unavailability, and mismatched energy are genuine factors at this stage of life. It’s perfectly okay to be grieving what dating used to look like, or what you hoped it might be at this stage of life.

It might be that you simply don’t want to date right now. And that is absolutely okay.

The Deeper Question

Here’s a deeper question beneath the question asked:

If dating were easy and required zero effort and the right person simply appeared, would you want a relationship?

Notice what comes up. Strip away all the obstacles with the apps, awkward first dates, or the fear of rejection. Would you want a relationship?

If your gut says yes, then what’s in your way is fear and logistics, both of which are things we can work with.

If your gut says I honestly don’t know, that’s worth exploring, perhaps with a coach like myself or a therapist, because ambivalence this profound usually means something deeper.

If your gut says no, I still wouldn’t want to date, you have your answer. Don’t second guess yourself. Dating is just not in the cards for you right now.

You’ve Built a Great Life. Is That Enough for You?

This woman has a build a good life. She has financial security, meaningful friendships, her own space, and a positive sense of self. She doesn’t need a relationship to complete her life.

And that is the best place to date from, if she chooses to.

But it’s also a perfectly good reason to pause. When your life is full, the bar for what a relationship would need to add gets higher, and that’s what I recommend…dating with discernment.

What About Intimacy?

She was honest about missing intimacy, and I don’t want to gloss over that. It’s real and it matters.

Intimacy is one of our most basic human needs. But what kind of intimacy are you longing for most? Physical closeness? Being truly known by someone? Having a partner to share daily life with? Someone to call when something good happens?

The answer shapes what you’re actually looking for, and whether a relationship with a man is the only path to getting it. Close friendships, physical affection (even platonic touch), and community can meet some of those needs. A relationship can meet others.

Also, if you’re craving the intimacy of a partner, dating apps are not the only solution. Start meeting more people in real life. Take a class. Go to a social event or a meetup. Baby steps to get out there without meeting on the apps.

Is it Fear or Frustration?

Probably both. And that’s okay.

The goal isn’t to force yourself into dating because you should want a relationship at 68. It’s to get honest with yourself about what you actually want, and then make a conscious choice rather than letting fear or inertia make it for you.

If you decide you want to try dating again, do it with open eyes and low stakes. Not because you need someone, but because you’re curious about what connection might look like in this next chapter.

And if you decide this chapter is about deepening what you already have, your friendships, your freedom, your relationship with yourself, that’s a great choice, too.

Either way, I want you to choose what works for you. On purpose. For yourself. Because you’re the only one who knows what’s best for you.

Do you have a dating dilemma you’d like answered on the blog and on Last First Date Radio? Submit yours here: https://tinyurl.com/datingdilemma

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If you’re feeling stuck in dating and relationships and would like to finally find love, apply for a complimentary 30-minute love breakthrough session with Sandy https://lastfirstdate.com/application

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Get a copy of Sandy’s books, Becoming a Woman of Value; How to Thrive in Life and Love and Choice Points in Dating; Empowering Women to Make Healthier Decisions in Love and Love at Last: True Stories of Falling in Love Later in Life

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